


The Cupid Complication

by SeeNashWrite



Category: Supernatural
Genre: F/M, Fluff, Friendship/Love, Gen, Holidays, Humor, valentines day
Language: English
Status: Completed
Published: 2019-02-15
Updated: 2019-02-15
Packaged: 2019-10-28 17:10:04
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,180
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/17791403
Author URL: https://archiveofourown.org/users/SeeNashWrite/pseuds/SeeNashWrite
Summary: During the Valentine season this year, complications arise for you & the Winchesters due to a cupid who could use some more practice at her job. A lot more practice. A *supreme* amount of practice.





	The Cupid Complication

The slow, methodical rapping sent a sharp, scolding noise into the air each time fingers hit desk.

_THRRRUMP_

_THRRRUMP_

_THRRRUMP_

Sinking lower into her seat, the cherub waited as her supervisor finished scanning the report.

The high-ranking angel behind the desk closed her eyes. The rapping stopped. She brought both hands up, now rubbing her temples. She sighed.

The cherub gulped.

“On your latest mission, your first arrow hit a statue, then your second, a tree, before successfully striking a human target upon your third attempt.”

"Y-yes, ma'am.”

“To be precise,  _with_ the third, you managed to hit  _three_ of them.”

“Uh… yes, ma'am. That’s funny, huh? But it only nicked the woman, I don’t think she was affected. See, what happened was—-”

“ _None_ of which were the assigned targets, that’s what I’m to understand?”

“Well, yes - I mean, no - I mean, yes, ma'am.”

“Octavia, I’ve repeatedly instructed you to  _not_ call me that.”

“Yes, m…. Okay.”

“Can you tell me why it is that we’ve navigated all the drama that is  _constantly_ plaguing heaven? Why we remain celestially adjacent?”

“Because we bring love to the world?” Octavia guessed.

“Because we - along with the muses and the reapers - specialize in the three things that will always be: life, death, and relationships. Those three things cannot be stopped, no matter how great a power may try to do so. They just  _are_. And what keeps things running smoothly amidst all the chaos?”

“Being good at our jobs?”

“Are you telling me, or asking me?” the supervisor snapped.

“I’m… I’m telling. That’s why.”

“That  _is_ why. We coordinate. We make sure the looms of the fates have nothing time-sensitive in store for our targets. We cross-check that they aren’t in the reapers’ queue. It is a finely-tuned machine. It is a flow. It is a rhythm. And you, Octavia, have continued to disrupt that rhythm, despite your missions being limited to the month of February, the easiest, the  _simplest_ month on the calendar for making matches.”

Octavia hung her head and picked at her glittery pink-polished fingernails.

It did not go unnoticed.

“While I have you here - I’ve let it slide, but your appearance—-”

“You told me I couldn’t be invisible except when I’m firing my bow! I’m trying to be festive for the season!” Octavia interjected, and was met with a stern  _look_.

“If you hadn’t materialized when you were marking that poor woman’s heart and grabbed her breast right there in the middle of that coffee shop—-”

“I wasn’t grabbing!” Octavia again interjected, and it was met with an even sterner  _look_. “It was a really soft sweater,” she mumbled sheepishly.

“ _That_ righteous ruckus, I remind you, is what got you downgraded back to arrows. And now I find myself wondering what to do with you, if you can’t even manage what new recruits seem to execute with accuracy!”

While her supervisor began adding notes to the sizable file on Octavia, the cherub caught a glance of herself in the mirror on the wall behind the desk. She thought she looked the part - her style was cheerful, and when she was visible and surveying, it made people smile, and she didn’t care what her co-workers said, not about her heart-patterned shirt, or the shiny red shoes, or the nail polish, or her hair.

 _“It’s pink!”_ they'd cried.

Octavia disagreed. Regardless of her form - big, small, skin tone, eye color - she always had wild, curly red hair. And not of a hue typically seen in nature; less ginger, more actual red. Actually, burgundy. Actually, it was possibly on the pink end of things. Fine, it was pink. But only in certain lighting. Besides, her clothes were needed - being naked was uncomfortable what with the oft-chafing quiver, so the clothing may as well match the hair - and besides  _that_ , Octavia was fine with the whole being-more-visible-than-not requirement. She liked being able to get to know her targets; even though the intel was always spot-on, it made her heart swell to know for sure she was making a good match.

They just didn’t understand. Most all cherubs - the cupids, at least - were less than enthused about Valentine’s Day, and Octavia couldn’t imagine why; after all, it was the holiday of  _love!_  And hopefully it was not spent alone, not if she had anything to do with it, despite the fact that Octavia herself often spent it alone. She didn’t have many friends… really, she didn’t have  _any_ friends. And so, her companions were her targets. And she loved them, all year ‘round.

Octavia was shaken from her thoughts when the file was slammed shut, and her eyes met the steely gaze of her supervisor once more.

“Your targets have been reassigned. You have a new assignment, which -  _if_  you succeed - means I won’t transfer you to…. to…. Oh, I don’t  _know_ where, but you’ll be  _gone_. Do you understand?”

“Ma’am? I mean, what? What is it? The assignment?” Octavia asked, nervous.

Her supervisor leaned across the desk, pointing a finger. “You are going to  _fix_ this.”

“How?”

“ _Think_ , Octavia. Who saw her first? Which of these—-“ A pause as the file was opened and papers were shuffled, followed by a huff when the sought information couldn’t be found immediately “—- _humans_ saw her first?” 

Octavia blinked, not following.

“The woman! You say she was only nicked, and if that’s true, you must focus on the other two - so  _Who. Saw. Her. First?_ ”

"It seemed both of them at once. They do lots of things in unison. It’s kind’ve weird.”

“Then I suppose you’ll have to figure out how to untangle this _weird_ one by _weird_ one. You have approximately twelve earth days - I want this  _done_ by sundown on the 14th. And without the bow, I don’t want to hear of any more stray shots.”

“But then how do I—-”

“Fix it.”

“But if you don’t want me to—-”

“ _FIX. IT._  Dismissed!”

Octavia stood, held out her arms for the customary goodbye handshake, but when the gesture was most decidedly  _not_ reciprocated, she slunk from the office.

After the door closed, the supervisor muttered under her breath as she dug around in her drawer for the small bottle of liquor she kept handy for such situations. Situations that most  _always_ involved Octavia. And as she sipped, she glanced back through the file. And then she blanched. And then she dropped her glass with a  _thunk_ onto the desk, causing the liquid to slosh across the paper, across the last names in the universe she’d have ever wanted to see.

_CONFIRMED HUMAN SUBJECTS INVOLVED IN INCIDENT, FEBRUARY 1st_

  * _WINCHESTER, DEAN  
_
  * _WINCHESTER, SAM_



_**~ Almost twelve days later ~**  
_.

“Can you help me with something?”

I glanced up from my research at the sound of Sam’s voice. “Of course,” I said, removing my glasses. “I need a break, anyway.”

In the kitchen, there was a small box on the table, wrapping paper, tape, scissors, and a ribbon lying next to it. And there was crumpled wrapping paper on the floor. A lot of crumpled wrapping paper. I looked from it to Sam, amused.

“I keep getting one side right, then the other side comes out all uneven when I fold it,” he explained. “And forget the bow, I wasn’t even gonna try.”

“No worries, I got you,” I told him, and plopped onto a seat. He sat across from me and watched as I picked up the paper and began to unroll it to judge the size. “So, is this for who I’m thinking?” I took a peek at Sam, caught the blush rising to his cheeks, and I grinned, having my answer. “You’ve been talking about her a lot since the last hunt.”

“Yeah, I guess I have,” he said. “I don’t know why, I just… started looking at her differently, you know?”

“Oh I know, and I get it, she’s great. And it’s nice to see you happy,” I said, about to lift the box - but then I stopped, met his eye. “Sam… this is leaking.”

“What?”

I pointed to the moisture trail the box had left when I’d pulled it closer. “Did you… you didn’t cook something, did you? I mean, that’s fine, it’s just we may need a different type of box, and no sense in wrapping it yet if it needs to be refrigerated, and—-”

Sam cut me off. “I didn’t cook anything - it’s a chocolate heart.”

We stared at each other for a moment, then stared down at the box, bewildered.

Which is when it jumped.

To be specific, it  _pulsed_ itself into the air, though only a tiny bit, shifting its position on the table slightly every time it came back down. Two successive plops, a brief moment, then it repeated. And it  _kept_ repeating. And it was on its fifth cycle before we came out of our shared daze, both putting our hands on the top to stop the movement. It vibrated under our palms.

“We gotta open it,” I said.

“What if it’s a cursed object?” Sam asked in response.

“Where the hell’d you get it?”

“Candy shop, same one that’s been on main street for forever, a little old lady owns it.”

“Witch, maybe?” I suggested.

We looked down as the box became a touch more aggressive in its pushback, the sides straining slightly - something thick was beginning to sneak out of the corners.

Sam shook his head, bewildered. “I dunno.”

“Well, whatever it is, it’s pissed off!” I announced and, as if it wanted to confirm my assertion, the box managed to knock our hands away, sending itself clean off the table and onto the floor, where it resumed its original soft bum-bum… bum- _bum_ …  _bum-bum…_

“It’s beating,” Sam said. “The heart.” A pause. “I can’t give her that!”

“THAT’S your concern?!” I shouted, then took a deep breath, exhaled it slowly, trying to quell my annoyance. “Okay. I’m opening it.”

“Wait! We should—” Sam began, but was interrupted.

“Hey, whoa - what’s going on, why’re you guys yelling?” Dean asked as he walked in, frowning.

The box performed its routine for him.

“Wow,” said Dean. “Never mind.” He looked to me. “I was gonna ask your opinion on something, but since you’re busy…”

I gave him a  _look_. “You’re in this now, too, bud.” I dropped into a squat, did a mental 1-2-3 count, and took the lid off the box.

“Gross,” Dean said, his nose wrinkling. “I mean, cool, but gross.”

“That’s not what I bought!” Sam said, pointing down at the cool-but-gross.

It was an actual, for real, no denying it, right there, in the box, human heart, and it was pumping out a brown, viscous fluid with every beat.

“Is that….” Sam said, but trailed off, and he squatted beside me, then dipped a finger into the goo. He held it to his nose, sniffed. “I think it’s chocolate.”

“Lemme see,” Dean said, and now he squatted, too - then to our horror, he dipped his finger as well, and immediately brought it to his lips, giving it a lick.

“Dean!” Sam and I exclaimed.

“Mmmm,” Dean hummed, his eyes closing briefly. “Oh, yeah. That’s the stuff.  _Good_ stuff. Is the rest made out of candy?”

“No!” Sam and I exclaimed.

Dean’s face went pinched again. “Gross,” he repeated, then promptly stood and began walking to the fridge. “I need a beer.”

“’I need a beer’, he says,” I commented, shaking my head.

Sam and I straightened ourselves, still watching the heart pump-pump away, but we looked back to Dean at the sound of chuckling.

“You may as well give it up, brother. I got you beat. Heh.  _Beat_ ,” he said with a smile, popping the cap off the beer.

“Beat at what?” I asked.

“Yeah, beat at  _what?_ ” Sam echoed, and the look on his face and his stiff posture and the way he crossed his arms and narrowed his eyes made me think he already knew what Dean meant.

“I mean, it’s creative, I’ll give you that - but chocolate’s not her favorite. Which you’d  _know_ , if you knew her as well as  _I_  do,” Dean replied, cool as could be.

It hit me then that Dean had  _also_ been talking about our hunter colleague an awful lot in the recent past, and it prompted me to ask, “Dean, what was it you wanted my opinion on?” **  
**

He swallowed a mouthful of beer, then replied, “I wanted to see what you thought about how my Valentine’s gift turned out.” Looking to Sam, he added, “Which I wrapped by myself.”

Sam looked like he wanted to smack the smug right off Dean’s face. “You did this!” he said. “You put some sort of hex on that heart - you’re trying to sabotage me!”

Dean rolled his eyes. “I don’t need to sabotage you, she’s not  _into_ you.”

Sam turned to me. “Years ago, over an autopsy, he passes me a human heart, just like that one—”

“No chocolate,” Dean pointed out.

“—and he said ‘Be my valentine’.”

“Dean… asked you… to be his valentine,” I said slowly.

“Not like— that’s not— it’s his sick sense of humor!” Sam explained. “And he’s doing it again! Trying to split us up!”

“Split  _who_ up?” I asked. “You’re not dating her!  _Neither_ of you are!”

“Not yet,” Dean said, still with the smug.

“What did you get her? Show me,” Sam demanded.

“Like I said, I got her favorite candy. C’mon,” Dean replied, setting down his beer and gesturing for us to follow.

As we walked down the hall to his room, they kept fussing, and as Dean was opening the door, I said, “You’re both acting really weird, I’m honestly getting concerned because—- good lord.”

A gift bag was tipped over on his bed, and what had to be dozens of worms were happily crawling around: on the bed itself, on the pillows, on the floor, on his desk, and - to his horror - over the stack of vintage porn mags on the nightstand.

“What the hell?!” he shouted.

Sam snickered.

The worms were fat, and glossy, and each segment was a color of the rainbow.

“Gummy worms?” I asked.

“Gummy worms,” Dean confirmed.

After a shared  _look_ \- the same one we’d share during hunts when we knew it was time to cut out and regroup - we all left the room, shutting the door behind us.

“You believe me now? That I’m not sabotaging you?” Dean asked Sam.

Sam nodded. “Yeah. Something’s up.”

“Finally!” I said. “We have to retrace our steps, figure out what caused this. Now, you two started talking about her on the way home after that hunt, I think, so—-”

“Something’s trying to keep me from her,” Dean and Sam stated in unison.

I groaned. “No, that’s  _not_ it - it’s that something’s, I dunno,  _infected_ the both of you, to make you want her. You know,  _want_ -her, want her.”

“I’m gonna go see her,” Dean said, determination all over his face and in his tone.

“Not if I get there first,” Sam replied, equally determined.

When they both began to move to, I assume, race each other to the car, I stood in the way. “Stop, okay? Isn’t she still up at Donna’s, going over traps and sigils with the girls?”

Dean got a moony smile on his face. “Man, she’s so freakin’ smart.”

Sam went dopey, too. “Right?  _So_ smart. Smartest person we know, definitely.”

“And the prettiest.”

“Pretty? She’s  _gorgeous_.”

“ _Totally_  the hottest chick we know.”

I raised my hand. “Hi? Right here, remember?”

Dean gave me an up-and-down. “You’re all right, you got nothing to worry about.”

“I’m. Not. Worried,” I said through grit teeth.

“And you’re good with the lore,” Sam offered halfheartedly.

“I  _know_. Look, if you’re gonna go up to Donna’s—-” I began, but they cut me off by going around me, headed toward the garage at what seemed like light speed. “I’m coming with you!” I yelled, hot on their heels, pausing only to snatch my jacket off the back of a library chair.

.

* * *

.

Thankfully, the road trip conversation was less argument and more fawning over the object of their mutual desire, and as much as I liked our friend, I got bored, which meant I got sleepy. In what felt like a blink of an eye, I suddenly found myself in the next county over from our destination. The slamming of the car doors had jolted me awake - according to my watch, they’d driven all through the night, the maniacs, and now it appeared a side mission had emerged.

We were parked in front of a liquor store.

It was surprisingly empty for Valentine’s Day, at least in my estimation. I’d have thought people would’ve been buying out the joint, last minute prep for their sappy candlelit dinners. I shuddered at the thought. That was me: Not Romantic, party of one.

When I entered, the gal behind the checkout counter gave me a polite smile and a small point in the direction of the refrigerated areas at the back of the store, to the only other occupants besides ourselves. But she didn’t need to - I’d heard them already. And it sounded like the most recent bout was about to hit a fever pitch.

“It’s the last one, and I got to it first!”

“Yeah, well I  _saw_ it first!”

Dean and Sam were yanking a bottle back and forth, and when I came up to them, I noted it was champagne.  _Pink_ champagne. I rolled my eyes, then reached in and snatched the bottle away, which earned me two dirty looks.

“Guys, I have a idea about what might’ve happened - is it possible this is a cupid situation?” I asked.

They both stared at me for a couple of seconds, and then smiles began to appear on both their faces.

“That explains it,” said Sam.

“It sure does,” said Dean.

I eyed both of them, suspicious at why they were pleased to hear my theory, but went on. “We should call Cas, see about doing a summoning spell.”

“We could do that on our own, I don’t wanna bother him while he’s spending time with Jack,” Sam replied.

I was instantly relieved - at least Sam was getting some sense.

“Why should we summon a cupid?” Dean asked. “If it _is_ a cupid, that must mean I’m meant to be with—-”

“Whoa, hold on,” Sam interrupted. “ _I’m_ supposed to be with—-”

So much for sense.

Now  _I_  interrupted. “What makes you think _either_ of you are supposed to be with her? Regardless, _both_ of you can’t be meant for her! This is obviously some sort of mistake!”

Dean’s lips curled into a smirk. “You jealous?”

My eyebrows shot up. “Jealous of  _what?_  Not being on the receiving end of leaky organs and creepy crawlers? Can we focus for a second? Back on the hunt, did you two see anybody that shouldn’t have been there? Before or after the salt and burn?”

“Nope,” Dean answered.

"Same here," Sam agreed.

I sighed. “Me, neither.” I thought a few more moments, then asked, “Anywhere else? Anybody new? Anybody  _unusual?_ ”

“Well, I mean… I guess the girl that sold me the heart was a little different. Different for Lebanon,” Sam said. “I’ve never seen her around town before, and I’d have noticed - she had pink hair.”

Dean nodded. “Uh-huh. Same girl sold me the worms. I’ve never seen her before, either.”

“Okay, so, pink hair - what else?” I asked.

“She was just… really Valentine-y. I thought it was just part of the sales shtick,” Dean answered.

“Yeah, her dress was patterned with these little lips, like kisses,” Sam said.

Dean gave him a  _look_ for remembering that piece of info, and I hid a smile.

Sam ignored him. “And she had a name you don’t hear often… it was Opal… Olive… Ophelia?”

Dean snapped his fingers. “No, no - it was, like, Octopus or something.”

“Octop—- Dean,  _what?_ ” Sam said, exasperated.

I ran a hand over my face, looked skyward for a second, briefly turning over in my mind how my life had come to this point, then brought my eyes back to them. “Was it Octavia?”

They were mildly stunned.

“How in the hell could you have known that?” Dean asked.

“Because I’m a hunter, and I’m observant, and I’m not in some whack-a-doo crazy cupid coma,” I replied, and I sounded snide, because I was being snide. “I know the  _name_ because of the  _name tag_.”

“I thought you didn’t see anybody at the cemetery,” Sam said, brow furrowed.

Dean frowned, as well. “And cupids wearing  _name tags?_  No they don’t, they’re naked. Where would they put it?”

“Oh my god, the stupid  _has_ to end,” I announced, and stepped behind him, grabbing his shoulders, shifting him so he was facing down the aisle, to the front of the store. I pointed. “Checkout girl? Up there? Pink sweater with white hearts? Pink-and-white striped skirt? Pink tights? Pink  _hair?!?_ ”

At that moment, the shelves began to tremble - specifically, the shelves lined with the  _not_ -pink champagne bottles. Glass clinked as they bumped into one another. The ones stored upright tipped onto their sides.

And then they fired.

Corks shot out like bullets, and we dodged and weaved, getting popped here-and-there, but other than sticky, bubble-coated boots, we managed to get out of the store unscathed. And on the sidewalk, we found her. There, the cotton candy-colored cupid stood, fidgeting, a hesitant smile on her face.

We stared.

“H-h-hi?” she managed.

We continued to stare.

“I screwed up,” she admitted. “And unless I fix this, I’ll be kicked out of the cupids.” Tears sprang to her already shining eyes. “I don’t even know what other cherubs  _do!_  And I don’t  _want_ to, I’m a  _good_ cupid, I  _am_.”

“Oh no. You suck,” Dean stated, and I frowned at him, gave him a sharp elbow, then looked to the source of our troubles.

“It’s Octavia, right?” I asked, glancing at the name tag.

She nodded. "I wouldn't lie."

I nodded in acknowledgement, and said, “Okay, then, keep that going. You need to tell us  _what_ , exactly, you screwed up.”

“I got the address backwards. I was supposed to be across town, not at that graveyard.” She paused, a contemplative expression coming to her face. “Now that I think of it, that isn’t a romantic place.”

“No,” Sam responded flatly. “It’s not.”

And then Octavia told her story, confirming my guess. “I thought all this would discourage you, but seems my arrows were more potent than I realized,” she finished. “I can’t tell you how sorry I am. You mean so much to me. Every one of you.”

Dean and Sam and I looked at each other, all of us softening - we believed her.

“Octavia, what else can be done?” Sam asked. “Because I’ll be honest, all I want to do right now is tackle Dean and steal the keys and leave him in the dust and go to her.”

“Awesome. Let's see you try,” Dean shot back, eyes narrowed, fists clenching.

I looked to the cupid with what I knew was desperation on my face as I moved to stand between the lovesick idiots.

“I could use something else on my arrows—-” Octavia began.

“NO ARROWS!” the three of us shouted.

“—-but it should work if you use it on yourselves.” She pulled three small bottles from the pocket of her skirt, all filled with a shimmery red liquid that gave off a slight golden glow.

“So do they drink it?” I asked.

Octavia shook her head. “It needs to be applied to where I hit them - well, Sam could maybe drink his, but…”

“But what?”

“But…  _butt_. I hit Dean in the butt, then it kind’ve curved up and hit Sam in the cheek. Not one of  _those_ cheeks, I mean—-”

I held up a hand. “Stop, I got it.”

Sam’s jaw dropped. “You’re— you’re telling me it went through his  _ass_ then in my  _mouth?_ ”

Dean leaned over, gripping his knees, laughing so hard he was gasping for breath in no time.

One of the bottles was smaller than the others, and after Octavia handed the first two to Sam and Dean, and they went back into the store to use it, she handed the tiny one to me.

“Give this to her, just in case. It’s for her arm. The arrow lost a lot of steam by the time it got to her, I think most of the juice was off it. Has she been calling a lot or did she show up at your place or anything?”

“Ah, that’s a big fat  _no_ ,” I answered. “All the crazy has been with these two. Lucky me.”

“You  _are_ lucky,” Octavia said. “My aim is so bad, I could’ve hit you, too. Then two of  _you_ could’ve been mismatched, along with that other woman, and it would’ve been worse.”

“Yeah… worse…” I said under my breath, my mind wandering for a moment. I shook myself out of it. “Well, look - no harm was done. Maybe a few bruises from your artillery in there, but otherwise we just have some clean-up to do back on the homefront. The candy stuff was pretty genius by the way.”

Octavia blushed. “You really think so?”

“Absolutely. And listen, I’m sure where you come from, they’ve got practice areas for shooting, right? That’s all you need. Hell, I had to practice every day for a  _long_  time before I got good at throwing blades. You’re creative, and you’re clearly passionate about your job. I don’t know what else heaven could ask for.”

A bright smile came to the cupid’s face. “Thank you. So much. I mean it.”

“So what’s on deck for you tonight, since you pulled this off? You gonna celebrate?” I asked.

“I don’t have any plans, it’s not like cupids have matchmakers, so… But I like being around love. I think I’ll hang out at that little restaurant around the corner, the people seemed happy there, and there’s paper hearts all taped on the windows, and I think I even saw some balloons. There’s no balloons in heaven.”

“Okay,” I said, and I smiled back, but I felt a little sad for her.

I didn’t have time to think on it for long - Dean and Sam emerged, and we all said our goodbyes.

.

* * *

.

The would-be paramour was packing up her car when we pulled up to Donna’s place, and after a brief round of rock-paper-scissors, Sam got the honor of explaining what had happened - a win or a loss, hard to tell.

But she was laughing through the whole story, and when it was done, she gave me a big hug, saying, “Bless your soul, I can’t imagine what it’s been like for you.”

I laughed, too. “Honestly, it wasn’t  _so_ awful. Plus, I get to bring this up every Valentine’s Day for years to come.”

“Great,” Dean said, not meaning it in the least.

“Do any of you have anything going on tonight?” she asked. “Should we go get a pizza or something on the way back to Kansas?”

“Nah, I think I’ll pass,” Dean said.

“Um, yeah. Me, too,” I said.

She turned to Sam. “How about you? I mean, why not make the best of it? And we don’t have to do pizza, we could do a movie, maybe?”

“You sure you’re feeling okay?” Sam asked hesitantly, which got another laugh out of her.

“Yes! If these two party poopers are out, that means we can watch something artsy they’d hate.”

Sam smiled, relieved. “Yeah, that actually sounds great.”

While they discussed their plans, Dean turned to me and said, “That’s not a half-bad idea.”

I was surprised. “What do you mean?”

“Making the best of it. We can go make with the best.”

“You wanna spend Valentine’s with me? I figured you’d… what happened to celebrating Lonely Ladies Getting Laid Day?”

“It’s Unattached Drifter Christmas. And I don’t mean anything  _fancy_ , or… stuff… It’s just… you know, as friends.”

That’s what he’d  _said_ , but he’d taken a step closer, and his voice had gotten a little softer, and if my eyes didn’t deceive me, the expression on his face held something I’d seldom seen on him: uncertainty.

“Friends?” I clarified.

“Well friends with be—-”

At my raised eyebrow, he cut himself off and course-corrected.

“Beer. Friends with  _beer_.”

“Uh-huh. Sure.”

“Sure…. sure, as in…. you’ll….”

“Sure, Dean. I’ll go.”

“You’ll go. Okay. Okay! That’s… that’s good, that’s…”

“Do I get flowers?” I asked casually, and at the near-horrified look on his face, tacked on a wink to let him know I was anything but serious.

He grinned. “You get a burger.”

I brought a hand to my chest. “Oh, Mr. Winchester - be still my heart.”

We were ready to get going, but after I filled him in on the rest of my conversation with our clumsy cupid, we agreed we had a quick stop to make before our Valentine’s Day evening got fully underway.

Octavia was at the bar nursing a cosmopolitan when the maître d’ approached.

“Miss? Might you be Octavia?”

She swallowed and said, “Yes? I mean, yes. That’s me.”

“This was just dropped off for you,” he said, handing her a plastic bag with a drugstore’s name across it. “Happy Valentine’s Day.”

Octavia took it, mumbling a thank you as he walked off, completely distracted; she’d never received a gift before. And it was the most perfect thing she’d ever seen. She knew well that most all the cards had long been sold, and she was glad, because this was much more special.

There it was, in her hands, her very own valentine, handmade with what materials were at their disposal. It was a cut-from-newspaper heart, trimmed in cotton balls, with random stickers that weren’t holiday-related but  _were_ all pinks-and-reds, stuck here-and-there around the writing. And that writing said:

.  
_Have a happy Valentine’s Day, Octavia. You deserve it. - Your favorite hunters  
__._

After swiping a few tears away, Octavia left money on the bar and upon exiting, scurried around to the back of the building so she could disappear. She needed to drop her valentine off back home. And she also needed to pick up something while she was there.

When she reached her final destination of the night, the cupid watched through the window of the burger joint for awhile, drinking in the happiness before her. It could mean trouble, what she was about to do, but in this case there wasn’t need for an assignment, or cross-checking with the fates or the reapers, because she felt it was right. She knew it, sparkled tips to shiny toes.

Tonight’s arrow was smaller, and coated delicately. Concentrating, Octavia aimed carefully. She didn’t blink, and she didn’t wobble, and for the first time ever she hit precisely the targets she intended.

It sailed clean through both their hearts, and Octavia smiled. They would have an amazing night. As for the rest, well - she’d leave forever up to them.

 

**Author's Note:**

> Feedback is fuel! Let me know if you enjoyed. -Nash
> 
> …And a quick PS: While you’ll notice standard divisions for change of scenes, the intro and ending are separated from this first-person perspective tale by the heart dividers, and are in third person for the purpose of giving the audience information that the main characters don’t know/don’t need to know - just FYI so you don’t think I’ve lost my mind… or my perspective, as it were. ;)


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